OCTREOTIDE HYDROCHLORIDE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C49H66N10O10S2.2ClH
Molecular Weight	1092.161
Optical Activity	UNSPECIFIED
Defined Stereocenters	10 / 10
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

Cl.Cl.C[C@@H](O)[C@@H](CO)NC(=O)[C@@H]1CSSC[C@H](NC(=O)[C@H](N)CC2=CC=CC=C2)C(=O)N[C@@H](CC3=CC=CC=C3)C(=O)N[C@H](CC4=CNC5=C4C=CC=C5)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H]([C@@H](C)O)C(=O)N1

InChI

InChIKey=PPJMKGDKFBCNIY-LODIGNQBSA-N

InChI=1S/C49H66N10O10S2.2ClH/c1-28(61)39(25-60)56-48(68)41-27-71-70-26-40(57-43(63)34(51)21-30-13-5-3-6-14-30)47(67)54-37(22-31-15-7-4-8-16-31)45(65)55-38(23-32-24-52-35-18-10-9-17-33(32)35)46(66)53-36(19-11-12-20-50)44(64)59-42(29(2)62)49(69)58-41;;/h3-10,13-18,24,28-29,34,36-42,52,60-62H,11-12,19-23,25-27,50-51H2,1-2H3,(H,53,66)(H,54,67)(H,55,65)(H,56,68)(H,57,63)(H,58,69)(H,59,64);2*1H/t28-,29-,34-,36+,37+,38-,39-,40+,41+,42+;;/m1../s1

HIDE SMILES / InChI

Molecular Formula	ClH
Molecular Weight	36.461
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Molecular Formula	C49H66N10O10S2
Molecular Weight	1019.239
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	10 / 10
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2012/019667s061lbl.pdf
Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/2876507 https://www.ncbi.nlm.nih.gov/pubmed/6128648

Octreotide (SMS 201-995, Sandostatin) is an octapeptide that exerts pharmacologic actions similar to the natural hormone, somatostatin. It was developed by Bauer and co-authors at Sandoz. It is an even more potent inhibitor of growth hormone, glucagon, and insulin than somatostatin. Like somatostatin, it also suppresses LH response to GnRH, decreases splanchnic blood flow, and inhibits release of serotonin, gastrin, vasoactive intestinal peptide, secretin, motilin, and pancreatic polypeptide. By virtue of these pharmacological actions, Sandostatin has been used to treat the symptoms associated with metastatic carcinoid tumors (flushing and diarrhea), and Vasoactive Intestinal Peptide (VIP) secreting adenomas (watery diarrhea). Sandostatin substantially reduces growth hormone and/or IGF-I (somatomedin C) levels in patients with acromegaly. A radioactively labelled analogue has been used to visualize somatostatin receptors in a GRF-secreting human tumour.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Somatostatin receptor 5 Target ID: CHEMBL2111436 Sources: http://www.kegg.jp/entry/D00442	Agonist 2678		1.7 nM [Kd]

Conditions

Condition	Modality	Highest Phase	Product
Acromegaly 21 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2012/019667s061lbl.pdf	Primary	Approved 8429	SANDOSTATIN Approved Use Acromegaly Sandostatin® (octreotide acetate) is indicated to reduce blood levels of growth hormone and IGF-I (somatomedin C) in acromegaly patients who have had inadequate response to or cannot be treated with surgical resection, pituitary irradiation, and bromocriptine mesylate at maximally tolerated doses. Launch Date 1988
Carcinoid tumors 4 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2012/019667s061lbl.pdf	Primary	Approved 8429	SANDOSTATIN Approved Use Carcinoid Tumors Sandostatin is indicated for the symptomatic treatment of patients with metastatic carcinoid tumors where it suppresses or inhibits the severe diarrhea and flushing episodes associated with the disease. Launch Date 1988
Vasoactive intestinal peptide tumors (VIPomas) 4 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2012/019667s061lbl.pdf	Primary	Approved 8429	SANDOSTATIN Approved Use Vasoactive Intestinal Peptide Tumors (VIPomas) Sandostatin is indicated for the treatment of the profuse watery diarrhea associated with VIP-secreting tumors. Launch Date 1988

C_max

Value	Dose	Co-administered	Analyte	Population
5.2 ng/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/213224s000lbl.pdf	100 μg single, subcutaneous dose: 100 μg route of administration: Subcutaneous experiment type: SINGLE co-administered:		OCTREOTIDE plasma	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN

AUC

Value	Dose	Co-administered	Analyte	Population
19 ng × h/mL DRUG LABEL https://pubmed.ncbi.nlm.nih.gov/22539587	20 mg single, oral dose: 20 mg route of administration: Oral experiment type: SINGLE co-administered:		OCTREOTIDE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

T_1/2

Value	Dose	Co-administered	Analyte	Population
0.2 h DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/213224s000lbl.pdf	100 μg single, subcutaneous dose: 100 μg route of administration: Subcutaneous experiment type: SINGLE co-administered:		OCTREOTIDE plasma	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN

F_unbound

Value	Dose	Co-administered	Analyte	Population
35% DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/213224s000lbl.pdf	100 μg single, subcutaneous dose: 100 μg route of administration: Subcutaneous experiment type: SINGLE co-administered:		OCTREOTIDE plasma	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1737

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
OATP1B1 788 OATP1B3 706 MRP2 383	P-gp 1537 MRP2 205

Drug as perpetrator

Target	Modality	Activity
MRP2 475	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/26330539/	weak [IC50 116.6 uM]
OATP1B3 715	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/26330539/	weak [IC50 68 uM]
OATP1B1 803	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/26330539/	yes [IC50 23 uM]

Drug as victim

Target	Modality	Activity
CYP3A4 1737	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/33407159/	yes
MRP2 205	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/33407159/	yes
P-gp 1537	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/33407159/	yes

Sourcing

Vendor/Aggregator	ID	URL
3B Scientific (Wuhan) Corp	3B2-1569	http://www.3bsc.com/index/pro_info.php?id=55285
AA Blocks	AA003A4T	https://www.aablocks.com/goods/Goods/detail?id=AA003A4T
AHH Chemical co.,ltd	MT-57470	http://www.ahhchemical.com/product/MT-57470.html
Aaron Chemicals	AR003AWL	http://www.aaronchem.com/83150-76-9
AbMole Bioscience	M5831	http://www.abmole.com/products/octreotide-acetate.html
Achemtek	0101-001239	http://www.achemtek.com/79517-01-4
Acorn PharmaTech	ACN-049497	http://www.acornpharmatech.com/
Alfa Chemistry	AP79517014	https://reagents.alfa-chemistry.com/product/octreotide-acetate-cas-79517-01-4-16671.html
Alfa Chemistry	AP83150769	https://reagents.alfa-chemistry.com/product/octreotide-cas-83150-76-9-17053.html
Angel Pharmatech	AG198758	http://www.angelpharmatech.com/83150-76-9.html
Ark Pharm	AK322030	http://www.arkpharminc.com/products/83150-76-9.html
Aurora Fine Chemicals LLC	A17.898.128	http://online.aurorafinechemicals.com/info?ID=A17.898.128
Aurora Fine Chemicals LLC	A18.033.422	http://online.aurorafinechemicals.com/info?ID=A18.033.422
AvaChem Scientific	2226	http://www.avachem.com/productSearch.asp?2226
BOC Sciences	79517-01-4	https://www.bocsci.com/octreotide-acetate-cas-79517-01-4-item-98609.html
BOC Sciences	83150-76-9	https://www.bocsci.com/octreotide-acetate-cas-83150-76-9-item-84-465327.html
BioChemPartner	BCP31200	http://www.biochempartner.com/1240797-41-4-BCP31200
BioChemPartner	BCP28870	http://www.biochempartner.com/83150-76-9-BCP28870
BioSynth	Q-201501	https://www.biosynth.com/en/products/life-science/other-biochemicals/products/Q-201501.html
CSNpharm	CSN20632	https://www.csnpharm.com/products/octreotide.html
ChemMol	49409410	http://www.chemmol.com/chemmol/49409410.html
ChemMol	99148044	http://www.chemmol.com/chemmol/99148044.html
ChemMol	99173353	http://www.chemmol.com/chemmol/99173353.html
ChemShuttle	104932	http://www.chemshuttle.com/catalogsearch/result/?q=83150-76-9&cat=
Chemenu	CM100710	http://www.chemenu.com/products/CM100710
Chemspace	CSSB00015189216	https://chem-space.com/CSSB00015189216
Chemspace	CSSB02125554369	https://chem-space.com/CSSB02125554369
DC Chemicals	DC12298	http://www.dcchemicals.com/product_show-Octreotide_acetate.html
Debye Scientific	DB-056369	http://www.debyesci.com/cas_79517-01-4.html
Finetech	FT-0630918	http://www.finetechnology-ind.com/prod/detail/pub/83150-76-9.html
Glentham Life Sciences	GP4360	http://www.glentham.com/products/product/GP4360/
Glentham Life Sciences	GP4986	http://www.glentham.com/products/product/GP4986/
Lab Network	LN01255188	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN01255188
Lab Network	LN01805767	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN01805767
Matrix Scientific	145269	https://www.matrixscientific.com/145269.html
MolPort	MolPort-009-194-181	https://www.molport.com/shop/molecule-link/MolPort-009-194-181
MolPort	MolPort-023-276-221	https://www.molport.com/shop/molecule-link/MolPort-023-276-221
MuseChem	I004901	https://www.musechem.com/product/I004901.html
OChem	7930	http://www.ocheminc.com/index.php?act=psearch&pid=17O014
Sigma-Aldrich	O1014_SIGMA	https://www.sigmaaldrich.com/catalog/product/sigma/o1014?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Smolecule	S537956	http://www.smolecule.com/products/s537956
THE BioTek	bt-278506	https://www.thebiotek.com/product/inhibitors/bt-278506
THE BioTek	bt-242340	https://www.thebiotek.com/product/peptides/bt-242340
Tocris	1818	https://www.tocris.com/products/octreotide_1818
Vitas-M Laboratory	STL483734	http://www.request.vitasmlab.com/index.php?option=com_search_stk&Itemid=22&stk=STL483734&?utm_source=pubchem&utm_medium=p_search_link&utm_campaign=pubchem_search&utm_content=pubchem_slink
abcr GmbH	AB493661	http://www.abcr.de/shop/en/AB493661
eNovation Chemicals	D371341	https://www.enovationchem.com/ProductDetails.asp?ProductID=D371341
eNovation Chemicals	D394708	https://www.enovationchem.com/ProductDetails.asp?ProductID=D394708
eNovation Chemicals	D587901	https://www.enovationchem.com/ProductDetails.asp?ProductID=D587901
eNovation Chemicals	D663565	https://www.enovationchem.com/ProductDetails.asp?ProductID=D663565
eNovation Chemicals	Y0974068	https://www.enovationchem.com/ProductDetails.asp?ProductID=Y0974068
iChemical	EBD23741	http://www.ichemical.com/products/79517-01-4.html?utm_source=PubChem&utm_medium=website&utm_campaign=product%20catalogs
iChemical	EBD2198093	http://www.ichemical.com/products/83150-76-9.html?utm_source=PubChem&utm_medium=website&utm_campaign=product%20catalogs

PubMed

Title	Date	PubMed
Review article: the relative effectiveness of somatostatin and octreotide therapy in pancreatic disease.	1995 Aug	8527611

Patents

Sample Use Guides

In Vivo Use Guide

Acromegaly: Dosage may be initiated at 50 mcg t.i.d. Beginning with this low dose may permit adaptation to adverse gastrointestinal effects for patients who will require higher doses. IGF-I (somatomedin C) levels every 2 weeks can be used to guide titration. Alternatively, multiple growth hormone levels at 0-8 hours after Sandostatin® (octreotide acetate) administration permit more rapid titration of dose. The goal is to achieve growth hormone levels less than 5 ng/mL or IGF-I (somatomedin C) levels less than 1.9 U/mL in males and less than 2.2 U/mL in females. The dose most commonly found to be effective is 100 mcg t.i.d., but some patients require up to 500 mcg t.i.d. for maximum effectiveness. Doses greater than 300 mcg/day seldom result in additional biochemical benefit, and if an increase in dose fails to provide additional benefit, the dose should be reduced. IGF-I (somatomedin C) or growth hormone levels should be re-evaluated at 6-month intervals. Carcinoid Tumors: The suggested daily dosage of Sandostatin during the first 2 weeks of therapy ranges from 100-600 mcg/day in 2-4 divided doses (mean daily dosage is 300 mcg). VIPomas: Daily dosages of 200-300 mcg in 2-4 divided doses are recommended during the initial 2 weeks of therapy (range 150-750 mcg) to control symptoms of the disease.

Route of Administration: Other

In Vitro Use Guide

1.25-20.0 nmol/ml (A2780/Taxol ovarian cancer cells)

Substance Class	Chemical Created by `admin` on `Sat Dec 16 06:18:22 GMT 2023` Edited by `admin` on `Sat Dec 16 06:18:22 GMT 2023`
Record UNII	H92K6Q47Q9
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

OCTREOTIDE HYDROCHLORIDE

Official Name

English

CAM-2029

Code

English

OCTREOTIDE DIHYDROCHLORIDE

Common Name

English

SMS995-AAA

Code

English

CAM2029

Code

English

SMS-995-AAA

Code

English

L-CYSTEINAMIDE, D-PHENYLALANYL-L-CYSTEINYL-L-PHENYLALANYL-D-TRYPTOPHYL-L-LYSYL-L-THREONYL-N-((1R,2R)-2-HYDROXY-1-(HYDROXYMETHYL)PROPYL)-, CYCLIC (2->7)-DISULFIDE, HYDROCHLORIDE (1:2)

Systematic Name

English

OCTREOTIDE HYDROCHLORIDE [USAN]

Common Name

English

OCTREOTIDE HYDROCHLORIDE, (-)-

Common Name

English

Octreotide hydrochloride [WHO-DD]

Common Name

English

Code System Code Type Description

PUBCHEM

91617941